Gemcitabine
Identification
- Summary
Gemcitabine is a nucleoside metabolic inhibitor used as adjunct therapy in the treatment of certain types of ovarian cancer, non-small cell lung carcinoma, metastatic breast cancer, and as a single agent for pancreatic cancer.
- Brand Names
- Gemzar, Infugem
- Generic Name
- Gemcitabine
- DrugBank Accession Number
- DB00441
- Background
Gemcitabine is a nucleoside analog and a chemotherapeutic agent. It was originally investigated for its antiviral effects, but it is now used as an anticancer therapy for various cancers.1 Gemcitabine is a cytidine analog with two fluorine atoms replacing the hydroxyl on the ribose.3 As a prodrug, gemcitabine is transformed into its active metabolites that work by replacing the building blocks of nucleic acids during DNA elongation, arresting tumour growth and promoting apoptosis of malignant cells.6 The structure, metabolism, and mechanism of action of gemcitabine are similar to cytarabine, but gemcitabine has a wider spectrum of antitumour activity.2
Gemcitabine is marketed as Gemzar and it is available as intravenous injection. It is approved by the FDA to treat advanced ovarian cancer in combination with carboplatin, metastatic breast cancer in combination with paclitaxel, non-small cell lung cancer in combination with cisplatin, and pancreatic cancer as monotherapy.4 It is also being investigated in other cancer and tumour types.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Gemcitabine (DB00441)
- Weight
- Average: 263.1981
Monoisotopic: 263.071762265 - Chemical Formula
- C9H11F2N3O4
- Synonyms
- 2'-Deoxy-2',2'-difluorocytidine
- 2',2'-Difluorodeoxycytidine
- 4-amino-1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidin-2(1H)-one
- Gemcitabin
- Gemcitabina
- Gemcitabine
- Gemcitabinum
- External IDs
- LY-188011
- LY188011
Pharmacology
- Indication
Gemcitabine is a chemotherapeutic agent used as monotherapy or in combination with other anticancer agents.
In combination with carboplatin, it is indicated for the treatment of advanced ovarian cancer that has relapsed at least 6 months after completion of platinum-based therapy.4
Gemcitabine in combination with paclitaxel is indicated for the first-line treatment of patients with metastatic breast cancer after failure of prior anthracycline-containing adjuvant chemotherapy, unless anthracyclines were clinically contraindicated.4
In combination with cisplatin, gemcitabine is indicated for the first-line treatment of patients with inoperable, locally advanced (Stage IIIA or IIIB) or metastatic (Stage IV) non-small cell lung cancer (NSCLC).4 Dual therapy with cisplatin is also used to treat patients with Stage IV (locally advanced or metastatic) transitional cell carcinoma (TCC) of the bladder.5
Gemcitabine is indicated as first-line treatment for patients with locally advanced (nonresectable Stage II or Stage III) or metastatic (Stage IV) adenocarcinoma of the pancreas. Gemcitabine is indicated for patients previously treated with fluorouracil.4
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- Advanced Non Small Cell Lung Cancer (NSCLC)
- Advanced Ovarian Cancer
- Bladder Transitional Cell Carcinoma Stage IV
- Cervical Cancers
- Cutaneous T Cell Lymphomas (CTCL)
- Head and Neck Carcinoma
- Hodgkins Disease (HD)
- Mesotheliomas
- Metastatic Breast Cancer
- Pancreatic Adenocarcinoma Locally Advanced
- Small Cell Lung Cancer (SCLC)
- Stage IIIA Non Small Cell Lung Cancer
- Stage IIIB Non Small Cell Lung Cancer
- Stage 4 Pancreatic adenocarcinoma
- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Gemcitabine is a nucleoside analog that mediates its antitumour effects by promoting apoptosis of malignant cells undergoing DNA synthesis. More specifically, it blocks the progression of cells through the G1/S-phase boundary.4 Gemcitabine demonstrated cytotoxic effects against a broad range of cancer cell lines in vitro. It displayed schedule-dependent antitumour activity in various animal models and xenografts from human non-small cell lung cancer (NSCLC) and pancreatic cancer.2 Therefore, the antineoplastic effects of gemcitabine are enhanced through prolonged infusion time rather than higher dosage.2 Gemcitabine inhibited the growth of human xenografts from carcinoma of the lung, pancreas, ovaries, head and neck, and breast. In mice, gemcitabine inhibited the growth of human tumour xenografts from the breast, colon, lung or pancreas by 69 to 99%. In clinical trials of advanced NSCLC, gemcitabine monotherapy produced objective response rates ranging from 18 to 26%, with a median duration of response ranging from 3.3 to 12.7 months. Overall median survival time was 6.2 to 12.3 months. The combined use of cisplatin and gemcitabine produced better objective response rates compared to monotherapy. In patients with advanced pancreatic cancer, objective response rates in patients ranged from 5.to 12%, with a median survival duration of 3.9 to 6.3 months.3 In Phase II trials involving patients with metastatic breast cancer, treatment with gemcitabine alone or with adjuvant chemotherapies resulted in response rate ranging from 13 to 42% and median survival duration ranging from 11.5 to 17.8 months. In metastatic bladder cancer, gemcitabine has a response rate 20 to 28%. In Phase II trials of advanced ovarian cancer, patients treated with gemcitabine had response rate of 57.1%, with progression free survival of 13.4 months and median survival of 24 months.2
Gemcitabine causes dose-limiting myelosuppression, such as anemia, leukopenia, neutropenia, and thrombocytopenia; however, events leading to discontinuation tend to occur less than 1% of the patients. Gemcitabine can elevate ALT, AST and alkaline phosphatase levels.3
- Mechanism of action
Gemcitabine is a potent and specific deoxycytidine analog. After uptake into malignant cells, gemcitabine is phosphorylated by deoxycytidine kinase to form gemcitabine monophosphate, which is then converted to the active compounds, gemcitabine diphosphate (dFdCDP) and gemcitabine triphosphate (dFdCTP). These active metabolites are nucleosides that mediate antitumour effects. dFdCTP competes with deoxycytidine triphosphate (dCTP) for incorporation into DNA, thereby competitively inhibiting DNA chain elongation. The non-terminal position of dFdCTP in the DNA chain prevents detection of dFdCTP in the chain and repair by proof-reading 3′5′-exonuclease: this process is referred to as "masked DNA chain termination." Incorporation of dFdCTP into the DNA chain ultimately leads to chain termination, DNA fragmentation, and apoptotic cell death of malignant cells.2,3,4
Gemcitabine has self-potentiating pharmacological actions that can increase the probability of successful incorporation of gemcitabine triphosphate into the DNA chain: dFdCDP inhibits ribonucleotide reductase, an enzyme responsible for catalyzing the reactions that generate dCTP for DNA synthesis. Since dFdCDP reduces the levels of dCTP, there is less competition for gemcitabine triphosphate for incorporation into DNA.2,4 Gemcitabine can also reduce metabolism and elimination of active metabolites from the target ce1l, prolonging high intracellular concentrations of the active metabolites. Such self-potentiating effects are not present with cytarabine.2
Target Actions Organism ADNA cross-linking/alkylationHumans ARibonucleoside-diphosphate reductase large subunit inhibitorHumans UThymidylate synthase inhibitorHumans UUMP-CMP kinase inhibitorHumans - Absorption
Peak plasma concentrations of gemcitabine range from 10 to 40 mg/L following a 30-minute intravenous infusion, and are reached at 15 to 30 minutes. One study showed that steady-state concentrations of gemcitabine showed a linear relationship to dose over the dose range 53 to 1000 mg/m2. Gemcitabine triphosphate, the active metabolite of gemcitabine, can accumulate in circulating peripheral blood mononuclear cells. In one study, the Cmax of gemcitabine triphosphate in peripheral blood mononuclear cells occurred within 30 minutes of the end of the infusion period and increased increased proportionally with gemcitabine doses of up to 350 mg/m2.2
- Volume of distribution
In patients with various solid tumours, the volume of distribution increased with infusion length. The volume of distribution of gemcitabine was 50 L/m2 following infusions lasting less than 70 minutes. For long infusions, the volume of distribution rose to 370 L/m2.4
Gemcitabine triphosphate, the active metabolite of gemcitabine, accumulates and retains in solid tumour cells in vitro and in vivo. It is not extensively distributed to tissues after short infusions that last less than 70 minutes.2 It is not known whether gemcitabine crosses the blood-brain barrier, but gemcitabine is widely distributed into tissues, including ascitic fluid.6 In rats, placental and lacteal transfer occurred rapidly at five to 15 minutes following drug administration.1
- Protein binding
Gemcitabine plasma protein binding is less than 10%.6
- Metabolism
Following administration and uptake into cancer cells, gemcitabine is initially phosphorylated by deoxycytidine kinase (dCK), and to a lower extent, the extra-mitochondrial thymidine kinase 2 to form gemcitabine monophosphate (dFdCMP). dFdCMP is subsequently phosphorylated by nucleoside kinases to form active metabolites, gemcitabine diphosphate (dFdCDP) and gemcitabine triphosphate (dFdCTP).3 Gemcitabine is also deaminated intracellularly and extracellularly by cytidine deaminase to its inactive metabolite 2′,2′-difluorodeoxyuridine or 2´-deoxy-2´,2´-difluorouridine (dFdU). Deamination occurs in the blood, liver, kidneys, and other tissues,1 and this metabolic pathway accounts for most of drug clearance.3,6
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- Route of elimination
Gemcitabine mainly undergoes renal excretion. Within a week following administration of a single dose of 1000 mg/m2 infused over 30 minutes, about 92-98% of the dose was recovered in urine where 89% of the recovered dose was excreted as difluorodeoxyuridine (dFdU) and less than 10% as gemcitabine.4 Monophosphate, diphosphate, or triphosphate metabolites of gemcitabine are not detectable in urine. In a single-dose study, about 1% of the administered dose was recovered in the feces.1
- Half-life
Following intravenous infusions lasting less than 70 minutes, the terminal half-life ranged from 0.7 to 1.6 hours. Following infusions ranging from 70 to 285 minutes, the terminal half-life ranged from 4.1 to 10.6 hours.6 Females tend to have longer half-lives than male patients. Gemcitabine triphosphate, the active metabolite of gemcitabine, can accumulate in circulating peripheral blood mononuclear cells. The terminal half-life of gemcitabine triphosphate, the active metabolite, from mononuclear cells ranges from 1.7 to 19.4 hours.4
- Clearance
Following intravenous infusions lasting less than 70 minutes, clearance ranged from 41 to 92 L/h/m2 in males and ranged from 31 to 69 L/h/m2 in females.6 Clearance decreases with age. Females have about 30% lower clearance than male patients.4
- Adverse Effects
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The oral LD50 is 333 mg/kg in mice and >500 mg/kg in rats. The dermal LD50 in rabbits is >1000 mg/kg.7
There is no known antidote for gemcitabine overdose. In a dose-escalation study, patients were administered a single dose of gemcitabine as high as 5700 mg/m2 administered by intravenous infusion over 30 minutes every two weeks: main observed toxicities were myelosuppression, paresthesia, and severe rash. In the event of a suspected drug overdose, blood counts should be monitored, and patients should be provided with supportive therapy, as necessary.4
- Pathways
Pathway Category Gemcitabine Metabolism Pathway Drug metabolism Gemcitabine Action Pathway Drug action - Pharmacogenomic Effects/ADRs
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Ribonucleoside-diphosphate reductase large subunit --- (A;A) A allele, homozygous / A allele, homozygous ADR Directly Studied Patients with this genotype have increased risk of neutropenia and neurotoxicity with gemcitabine. Details
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Gemcitabine may decrease the excretion rate of Abacavir which could result in a higher serum level. Abatacept The risk or severity of adverse effects can be increased when Gemcitabine is combined with Abatacept. Abciximab The risk or severity of bleeding can be increased when Abciximab is combined with Gemcitabine. Abemaciclib The serum concentration of Abemaciclib can be increased when it is combined with Gemcitabine. Aceclofenac Aceclofenac may decrease the excretion rate of Gemcitabine which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Gemcitabine which could result in a higher serum level. Acenocoumarol The therapeutic efficacy of Acenocoumarol can be increased when used in combination with Gemcitabine. Acetaminophen Acetaminophen may decrease the excretion rate of Gemcitabine which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Gemcitabine which could result in a lower serum level and potentially a reduction in efficacy. Acetylsalicylic acid The risk or severity of bleeding can be increased when Acetylsalicylic acid is combined with Gemcitabine. 
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- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Gemcitabine hydrochloride U347PV74IL 122111-03-9 OKKDEIYWILRZIA-OSZBKLCCSA-N - International/Other Brands
- Abine (Dosa) / Abingem (Miracalus) / Acytabin (Intas) / Celgem (Alkem) / Celzar (Celon) / Cytogem (Dr Reddys) / Daplax (Dr Reddys) / Dercin (Egis) / Eriogem (Eriochem) / Fotinex (Fada) / Gebina (Aspen) / Gembio (Bioprofarma) / Gemcired (Dr Reddys) / Gemita (Fresenius) / Gezt (Richmond) / Gitrabin (Actavis) / Gramagen (Lilly) / Jemta (Sandoz) / Nallian (Gedeon Richter) / Oncogem (Grey Inversiones) / Ribozar (Ribosepharm) / Tabin (Crinos) / Xtroz (Ranbaxy)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Act Gemcitabine Powder, for solution 200 mg / vial Intravenous Actavis Pharma Company Not applicable Not applicable Canada 
Act Gemcitabine Powder, for solution 1 g / vial Intravenous Actavis Pharma Company Not applicable Not applicable Canada Act Gemcitabine Solution 38 mg / mL Intravenous Actavis Pharma Company 2016-05-02 2019-08-13 Canada Gemcitabine Injection, solution 38 mg/1mL Intravenous Hospira, Inc. 2011-08-26 Not applicable US 
Gemcitabine Injection, solution 100 mg/1mL Intravenous BluePoint Laboratories 2018-05-25 Not applicable US Gemcitabine Injection, solution 100 mg/1mL Intravenous BluePoint Laboratories 2018-05-25 Not applicable US Gemcitabine Injection, solution 100 mg/1mL Intravenous Accord Healthcare Inc. 2018-01-24 Not applicable US Gemcitabine Injection, solution 38 mg/1mL Intravenous Hospira, Inc. 2011-08-24 Not applicable US Gemcitabine Injection, solution 100 mg/1mL Intravenous BluePoint Laboratories 2018-05-25 Not applicable US Gemcitabine Injection, solution 38 mg/1mL Intravenous Mylan Laboratories Limited 2017-12-31 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Aj-gemcitabine Powder, for solution 200 mg / vial Intravenous Agila Jamp Canada Inc Not applicable Not applicable Canada Aj-gemcitabine Powder, for solution 2 g / vial Intravenous Agila Jamp Canada Inc Not applicable Not applicable Canada Aj-gemcitabine Powder, for solution 1 g / vial Intravenous Agila Jamp Canada Inc Not applicable Not applicable Canada Gemcitabine Injection, solution 200 mg/5.26mL Intravenous Mylan Institutional LLC 2018-01-03 Not applicable US Gemcitabine Injection, powder, lyophilized, for solution 2 g/50mL Intravenous Fresenius Kabi USA, LLC 2011-05-17 Not applicable US Gemcitabine Injection, powder, lyophilized, for solution 38 mg/1mL Intravenous Hospira, Inc. 2011-07-26 Not applicable US Gemcitabine Injection, powder, lyophilized, for solution 1 g/1 Intravenous Shilpa Medicare Limited 2018-06-06 Not applicable US Gemcitabine Injection, powder, lyophilized, for solution 1 g/25mL Intravenous Sagent Pharmaceuticals 2011-07-25 2017-07-31 US Gemcitabine Injection, solution 38 mg/1mL Intravenous Apotex Corp. 2018-03-20 2021-01-31 US Gemcitabine Injection, powder, lyophilized, for solution 1 g/1 Intravenous Meitheal Pharmaceuticals Inc. 2018-11-01 Not applicable US
Categories
- ATC Codes
- L01BC05 — Gemcitabine
- Drug Categories
- Antimetabolites
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- Carbohydrates
- Cytidine Deaminase Substrates
- Deoxyribonucleosides
- Drugs that are Mainly Renally Excreted
- Enzyme Inhibitors
- Glycosides
- Immunosuppressive Agents
- Myelosuppressive Agents
- Narrow Therapeutic Index Drugs
- Noxae
- Nucleic Acid Synthesis Inhibitors
- Nucleic Acids, Nucleotides, and Nucleosides
- Nucleoside Metabolic Inhibitor
- Nucleosides
- P-glycoprotein substrates
- P-glycoprotein substrates with a Narrow Therapeutic Index
- Pyrimidine Analogues
- Pyrimidine Nucleosides
- Pyrimidines
- Ribonucleosides
- Ribonucleotide Reductases, antagonists & inhibitors
- Toxic Actions
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. These are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.
- Kingdom
- Organic compounds
- Super Class
- Nucleosides, nucleotides, and analogues
- Class
- Pyrimidine nucleosides
- Sub Class
- Pyrimidine 2'-deoxyribonucleosides
- Direct Parent
- Pyrimidine 2'-deoxyribonucleosides
- Alternative Parents
- Pyrimidones / Aminopyrimidines and derivatives / Hydropyrimidines / Imidolactams / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols / Fluorohydrins / Azacyclic compounds / Oxacyclic compounds show 7 more
- Substituents
- Alcohol / Alkyl fluoride / Alkyl halide / Amine / Aminopyrimidine / Aromatic heteromonocyclic compound / Azacycle / Fluorohydrin / Halohydrin / Heteroaromatic compound show 20 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- organofluorine compound, pyrimidine 2'-deoxyribonucleoside (CHEBI:175901)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- B76N6SBZ8R
- CAS number
- 95058-81-4
- InChI Key
- SDUQYLNIPVEERB-QPPQHZFASA-N
- InChI
- InChI=1S/C9H11F2N3O4/c10-9(11)6(16)4(3-15)18-7(9)14-2-1-5(12)13-8(14)17/h1-2,4,6-7,15-16H,3H2,(H2,12,13,17)/t4-,6-,7-/m1/s1
- IUPAC Name
- 4-amino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
- SMILES
- NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](CO)[C@@H](O)C1(F)F
References
- Synthesis Reference
John A. Weigel, "Process for making gemcitabine hydrochloride." U.S. Patent US6001994, issued May, 1995.
US6001994- General References
- Noble S, Goa KL: Gemcitabine. A review of its pharmacology and clinical potential in non-small cell lung cancer and pancreatic cancer. Drugs. 1997 Sep;54(3):447-72. doi: 10.2165/00003495-199754030-00009. [Article]
- Toschi L, Finocchiaro G, Bartolini S, Gioia V, Cappuzzo F: Role of gemcitabine in cancer therapy. Future Oncol. 2005 Feb;1(1):7-17. doi: 10.1517/14796694.1.1.7. [Article]
- Ciccolini J, Serdjebi C, Peters GJ, Giovannetti E: Pharmacokinetics and pharmacogenetics of Gemcitabine as a mainstay in adult and pediatric oncology: an EORTC-PAMM perspective. Cancer Chemother Pharmacol. 2016 Jul;78(1):1-12. doi: 10.1007/s00280-016-3003-0. Epub 2016 Mar 23. [Article]
- FDA Approved Drug Products: GEMZAR (gemcitabine) for injection, for intravenous use [Link]
- Product Monograph: GEMCITABINE Intravenous Injection [Link]
- BC Cancer: Gemcitabine Monograph [Link]
- Pfizer: Gemcitabine Safety Data Sheet [Link]
- External Links
- Human Metabolome Database
- HMDB0014584
- KEGG Drug
- D02368
- KEGG Compound
- C07650
- PubChem Compound
- 60750
- PubChem Substance
- 46506425
- ChemSpider
- 54753
- BindingDB
- 429521
- 12574
- ChEBI
- 175901
- ChEMBL
- CHEMBL888
- ZINC
- ZINC000018279854
- Therapeutic Targets Database
- DAP001246
- PharmGKB
- PA449748
- PDBe Ligand
- GEO
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Gemcitabine
- PDB Entries
- 1p62 / 2no0 / 2vpp / 4pd5 / 6nl4
- FDA label
- Download (105 KB)
- MSDS
- Download (69.2 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Non Small Cell Lung Cancer Squamous (NSCLC-Sq) 1 4 Completed Treatment Adenocarcinomas of the Pancreas 1 4 Completed Treatment Non-Small Cell Lung Carcinoma (NSCLC) 2 4 Not Yet Recruiting Treatment Metastatic Non-Small Cell Lung Cancer 1 4 Recruiting Treatment Hemophagocytic Syndrome (HPS) / T/NK-Cell Lymphoma 1 4 Recruiting Treatment Pancreatic Adenocarcinoma (Ductal Adenocarcinoma) 1 4 Recruiting Treatment Peripheral T Cell Lymphoma (PTCL) 2 4 Terminated Treatment EGFR Activating Mutation / Metastatic Non-Small Cell Lung Cancer 1 4 Terminated Treatment Malignant Neoplasm of Pancreas 1 4 Terminated Treatment Renal Cell Adenocarcinoma 1
Pharmacoeconomics
- Manufacturers
- Teva parenteral medicines inc
- Eli lilly and co
- Packagers
- Eli Lilly & Co.
- Dosage Forms
Form Route Strength Solution Intravenous 38 mg / mL Injection Intravenous 1 G Powder, for solution Injection, solution, concentrate Intravenous; Parenteral 40 MG/ML Solution Intravenous 1 g Injection, solution, concentrate Intravenous Injection, powder, for solution Parenteral Solution Intravenous 10 mg Solution, concentrate Intravenous 10 mg Injection, powder, lyophilized, for solution Intravenous 1 g Injection, powder, lyophilized, for solution Intravenous 200 mg Solution Intravenous 40 mg Injection, solution, concentrate Intravenous; Parenteral 100 MG/ML Powder, for solution Intravenous 38 MG/ML Powder, for solution Parenteral 38 MG/ML Powder, for solution Parenteral 1 G Powder, for solution Parenteral 2 G Powder, for solution Parenteral 200 MG Injection, solution, concentrate Intravenous; Parenteral 38 MG/ML Injection, solution Parenteral 10 MG/ML Injection Intravenous 1 g/26.3mL Injection Intravenous 2 g/52.6mL Injection Intravenous 200 mg/5.26mL Injection Intravenous 38 mg/1mL Injection, powder, for solution Intravenous 200 MG Injection, powder, lyophilized, for solution Intravenous 1 g/1 Injection, powder, lyophilized, for solution Intravenous 200 mg/1 Injection, powder, lyophilized, for solution Intravenous 40 mg/1mL Injection, solution Intravenous 1 g/26.3mL Injection, solution Intravenous 100 mg/1mL Injection, solution Intravenous 2 g/52.6mL Injection, solution Intravenous 200 mg/5.26mL Injection, solution Intravenous 38 mg/1mL Injection Intravenous Powder, for solution Intravenous 1 g / vial Powder, for solution Intravenous 200 mg / vial Solution Intravenous 100 mg / mL Injection, powder, for solution 1000 mg/1vial Powder Intravenous 1 g / vial Powder Intravenous 2 g / vial Powder Intravenous 200 mg / vial Powder, for solution Intravenous 2 g / vial Injection, powder, lyophilized, for solution Intravenous 1 g/25mL Injection, powder, lyophilized, for solution Intravenous 200 mg/5mL Solution Intravenous Injection, powder, lyophilized, for solution Intravenous 2 g/50mL Injection, powder, lyophilized, for solution Intravenous 38 mg/1mL Solution Intravenous 40 mg / mL Injection, powder, for solution Intravenous Powder Intravenous 1000 mg/1vial Powder Intravenous 200 mg/1vial Injection, powder, lyophilized, for solution Intravenous 200 mg/1vial Injection, solution Intravenous Injection, powder, lyophilized, for solution Intravenous Injection, powder, for solution 200 mg/1vial Injection, solution, concentrate Parenteral Injection, powder, for solution Intravenous 1 g Cream Injection, powder, for solution Injection, solution Intravenous 10 mg/1mL Injection, solution, concentrate Intravenous 38 MG/ML Solution, concentrate Intravenous 38 mg Injection, powder, lyophilized, for solution Intravenous 1000 mg Powder Intravenous 1400 mg/1vial Injection, powder, lyophilized, for solution Intravenous 1000 mg/1vial - Prices
Unit description Cost Unit Gemzar 1 gm Solution Vial 903.93USD vial Gemzar 1 gram vial 869.16USD vial Gemzar 200 mg Solution Vial 180.78USD vial DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5464826 No 1995-11-07 2013-05-07 US US4808614 No 1989-02-28 2010-05-15 US US9241948 No 2016-01-26 2033-07-01 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility 15.3 g/L https://cdn.pfizer.com/pfizercom/products/material_safety_data/Gemcitabine_Injection_(Hospira)16-Nov-2016.pdf logP -1.4 Not Available pKa 3.6 Not Available - Predicted Properties
Property Value Source Water Solubility 22.3 mg/mL ALOGPS logP 0.14 ALOGPS logP -1.5 ChemAxon logS -1.1 ALOGPS pKa (Strongest Acidic) 11.52 ChemAxon pKa (Strongest Basic) 3.65 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 108.38 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 53.25 m3·mol-1 ChemAxon Polarizability 21.62 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9814 Blood Brain Barrier + 0.9693 Caco-2 permeable - 0.8957 P-glycoprotein substrate Non-substrate 0.8317 P-glycoprotein inhibitor I Non-inhibitor 0.9557 P-glycoprotein inhibitor II Non-inhibitor 0.9106 Renal organic cation transporter Non-inhibitor 0.939 CYP450 2C9 substrate Non-substrate 0.8634 CYP450 2D6 substrate Non-substrate 0.8484 CYP450 3A4 substrate Non-substrate 0.6016 CYP450 1A2 substrate Non-inhibitor 0.8958 CYP450 2C9 inhibitor Non-inhibitor 0.8633 CYP450 2D6 inhibitor Non-inhibitor 0.8787 CYP450 2C19 inhibitor Non-inhibitor 0.8478 CYP450 3A4 inhibitor Non-inhibitor 0.9032 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8862 Ames test Non AMES toxic 0.6793 Carcinogenicity Non-carcinogens 0.8286 Biodegradation Not ready biodegradable 0.9948 Rat acute toxicity 2.1220 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9948 hERG inhibition (predictor II) Non-inhibitor 0.8314
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
References
- Hastak K, Alli E, Ford JM: Synergistic chemosensitivity of triple-negative breast cancer cell lines to poly(ADP-Ribose) polymerase inhibition, gemcitabine, and cisplatin. Cancer Res. 2010 Oct 15;70(20):7970-80. doi: 10.1158/0008-5472.CAN-09-4521. Epub 2010 Aug 26. [Article]
- Ledermann JA, Gabra H, Jayson GC, Spanswick VJ, Rustin GJ, Jitlal M, James LE, Hartley JA: Inhibition of carboplatin-induced DNA interstrand cross-link repair by gemcitabine in patients receiving these drugs for platinum-resistant ovarian cancer. Clin Cancer Res. 2010 Oct 1;16(19):4899-905. doi: 10.1158/1078-0432.CCR-10-0832. Epub 2010 Aug 18. [Article]
- Garcia-Diaz M, Murray MS, Kunkel TA, Chou KM: Interaction between DNA Polymerase lambda and anticancer nucleoside analogs. J Biol Chem. 2010 May 28;285(22):16874-9. doi: 10.1074/jbc.M109.094391. Epub 2010 Mar 26. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- Curator comments
- This enzyme is inhibited by the active metabolite of gemcitabine, gemcitabine diphosphate.
- General Function
- Ribonucleoside-diphosphate reductase activity, thioredoxin disulfide as acceptor
- Specific Function
- Provides the precursors necessary for DNA synthesis. Catalyzes the biosynthesis of deoxyribonucleotides from the corresponding ribonucleotides.
- Gene Name
- RRM1
- Uniprot ID
- P23921
- Uniprot Name
- Ribonucleoside-diphosphate reductase large subunit
- Molecular Weight
- 90069.375 Da
References
- Kwon WS, Rha SY, Choi YH, Lee JO, Park KH, Jung JJ, Kim TS, Jeung HC, Chung HC: Ribonucleotide reductase M1 (RRM1) 2464G>A polymorphism shows an association with gemcitabine chemosensitivity in cancer cell lines. Pharmacogenet Genomics. 2006 Jun;16(6):429-38. [Article]
- Rosell R, Cobo M, Isla D, Camps C, Massuti B: Pharmacogenomics and gemcitabine. Ann Oncol. 2006 May;17 Suppl 5:v13-16. [Article]
- Bepler G, Kusmartseva I, Sharma S, Gautam A, Cantor A, Sharma A, Simon G: RRM1 modulated in vitro and in vivo efficacy of gemcitabine and platinum in non-small-cell lung cancer. J Clin Oncol. 2006 Oct 10;24(29):4731-7. Epub 2006 Sep 11. [Article]
- Smid K, Bergman AM, Eijk PP, Veerman G, van Haperen VW, van den Ijssel P, Ylstra B, Peters GJ: Micro-array analysis of resistance for gemcitabine results in increased expression of ribonucleotide reductase subunits. Nucleosides Nucleotides Nucleic Acids. 2006;25(9-11):1001-7. [Article]
- Nakahira S, Nakamori S, Tsujie M, Takahashi Y, Okami J, Yoshioka S, Yamasaki M, Marubashi S, Takemasa I, Miyamoto A, Takeda Y, Nagano H, Dono K, Umeshita K, Sakon M, Monden M: Involvement of ribonucleotide reductase M1 subunit overexpression in gemcitabine resistance of human pancreatic cancer. Int J Cancer. 2007 Mar 15;120(6):1355-63. [Article]
- Cerqueira NM, Fernandes PA, Ramos MJ: Understanding ribonucleotide reductase inactivation by gemcitabine. Chemistry. 2007;13(30):8507-15. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Thymidylate synthase activity
- Specific Function
- Contributes to the de novo mitochondrial thymidylate biosynthesis pathway.
- Gene Name
- TYMS
- Uniprot ID
- P04818
- Uniprot Name
- Thymidylate synthase
- Molecular Weight
- 35715.65 Da
References
- Rosell R, Taron M, Sanchez JM, Moran T, Reguart N, Besse B, Isla D, Massuti B, Alberola V, Sanchez JJ: The promise of pharmacogenomics: gemcitabine and pemetrexed. Oncology (Williston Park). 2004 Nov;18(13 Suppl 8):70-6. [Article]
- Huang CL, Yokomise H, Fukushima M, Kinoshita M: Tailor-made chemotherapy for non-small cell lung cancer patients. Future Oncol. 2006 Apr;2(2):289-99. [Article]
- Giovannetti E, Mey V, Nannizzi S, Pasqualetti G, Marini L, Del Tacca M, Danesi R: Cellular and pharmacogenetics foundation of synergistic interaction of pemetrexed and gemcitabine in human non-small-cell lung cancer cells. Mol Pharmacol. 2005 Jul;68(1):110-8. Epub 2005 Mar 28. [Article]
- Zhao XD, Zhang Y: [Routine chemotherapeutic drug treatment effectiveness predictive molecules and chemotherapeutic drug selection]. Ai Zheng. 2006 Dec;25(12):1577-80. [Article]
- Giovannetti E, Mey V, Nannizzi S, Pasqualetti G, Del Tacca M, Danesi R: Pharmacogenetics of anticancer drug sensitivity in pancreatic cancer. Mol Cancer Ther. 2006 Jun;5(6):1387-95. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Marce S, Molina-Arcas M, Villamor N, Casado FJ, Campo E, Pastor-Anglada M, Colomer D: Expression of human equilibrative nucleoside transporter 1 (hENT1) and its correlation with gemcitabine uptake and cytotoxicity in mantle cell lymphoma. Haematologica. 2006 Jul;91(7):895-902. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Uridylate kinase activity
- Specific Function
- Catalyzes the phosphorylation of pyrimidine nucleoside monophosphates at the expense of ATP. Plays an important role in de novo pyrimidine nucleotide biosynthesis. Has preference for UMP and CMP as...
- Gene Name
- CMPK1
- Uniprot ID
- P30085
- Uniprot Name
- UMP-CMP kinase
- Molecular Weight
- 22222.175 Da
References
- Vernejoul F, Ghenassia L, Souque A, Lulka H, Drocourt D, Cordelier P, Pradayrol L, Pyronnet S, Buscail L, Tiraby G: Gene therapy based on gemcitabine chemosensitization suppresses pancreatic tumor growth. Mol Ther. 2006 Dec;14(6):758-67. Epub 2006 Sep 25. [Article]
- Hsu CH, Liou JY, Dutschman GE, Cheng YC: Phosphorylation of Cytidine, Deoxycytidine, and Their Analog Monophosphates by Human UMP/CMP Kinase Is Differentially Regulated by ATP and Magnesium. Mol Pharmacol. 2005 Mar;67(3):806-14. Epub 2004 Nov 18. [Article]
- Maring JG, Groen HJ, Wachters FM, Uges DR, de Vries EG: Genetic factors influencing pyrimidine-antagonist chemotherapy. Pharmacogenomics J. 2005;5(4):226-43. [Article]
- Lam W, Leung CH, Bussom S, Cheng YC: The impact of hypoxic treatment on the expression of phosphoglycerate kinase and the cytotoxicity of troxacitabine and gemcitabine. Mol Pharmacol. 2007 Sep;72(3):536-44. Epub 2007 Jun 12. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Zinc ion binding
- Specific Function
- This enzyme scavenges exogenous and endogenous cytidine and 2'-deoxycytidine for UMP synthesis.
- Gene Name
- CDA
- Uniprot ID
- P32320
- Uniprot Name
- Cytidine deaminase
- Molecular Weight
- 16184.545 Da
References
- Giovannetti E, Laan AC, Vasile E, Tibaldi C, Nannizzi S, Ricciardi S, Falcone A, Danesi R, Peters GJ: Correlation between cytidine deaminase genotype and gemcitabine deamination in blood samples. Nucleosides Nucleotides Nucleic Acids. 2008 Jun;27(6):720-5. doi: 10.1080/15257770802145447. [Article]
- Gusella M, Pasini F, Bolzonella C, Meneghetti S, Barile C, Bononi A, Toso S, Menon D, Crepaldi G, Modena Y, Stievano L, Padrini R: Equilibrative nucleoside transporter 1 genotype, cytidine deaminase activity and age predict gemcitabine plasma clearance in patients with solid tumours. Br J Clin Pharmacol. 2011 Mar;71(3):437-44. doi: 10.1111/j.1365-2125.2010.03838.x. [Article]
- Wong A, Soo RA, Yong WP, Innocenti F: Clinical pharmacology and pharmacogenetics of gemcitabine. Drug Metab Rev. 2009;41(2):77-88. doi: 10.1080/03602530902741828. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Protein homodimerization activity
- Specific Function
- Required for the phosphorylation of the deoxyribonucleosides deoxycytidine (dC), deoxyguanosine (dG) and deoxyadenosine (dA). Has broad substrate specificity, and does not display selectivity based...
- Gene Name
- DCK
- Uniprot ID
- P27707
- Uniprot Name
- Deoxycytidine kinase
- Molecular Weight
- 30518.315 Da
References
- Wong A, Soo RA, Yong WP, Innocenti F: Clinical pharmacology and pharmacogenetics of gemcitabine. Drug Metab Rev. 2009;41(2):77-88. doi: 10.1080/03602530902741828. [Article]
- Marechal R, Mackey JR, Lai R, Demetter P, Peeters M, Polus M, Cass CE, Salmon I, Deviere J, Van Laethem JL: Deoxycitidine kinase is associated with prolonged survival after adjuvant gemcitabine for resected pancreatic adenocarcinoma. Cancer. 2010 Nov 15;116(22):5200-6. doi: 10.1002/cncr.25303. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Thymidine kinase activity
- Specific Function
- Deoxyribonucleoside kinase that phosphorylates thymidine, deoxycytidine, and deoxyuridine. Also phosphorylates anti-viral and anti-cancer nucleoside analogs.
- Gene Name
- TK2
- Uniprot ID
- O00142
- Uniprot Name
- Thymidine kinase 2, mitochondrial
- Molecular Weight
- 31004.53 Da
References
- Ciccolini J, Serdjebi C, Peters GJ, Giovannetti E: Pharmacokinetics and pharmacogenetics of Gemcitabine as a mainstay in adult and pediatric oncology: an EORTC-PAMM perspective. Cancer Chemother Pharmacol. 2016 Jul;78(1):1-12. doi: 10.1007/s00280-016-3003-0. Epub 2016 Mar 23. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Uridylate kinase activity
- Specific Function
- Catalyzes the phosphorylation of pyrimidine nucleoside monophosphates at the expense of ATP. Plays an important role in de novo pyrimidine nucleotide biosynthesis. Has preference for UMP and CMP as...
- Gene Name
- CMPK1
- Uniprot ID
- P30085
- Uniprot Name
- UMP-CMP kinase
- Molecular Weight
- 22222.175 Da
References
- Ciccolini J, Serdjebi C, Peters GJ, Giovannetti E: Pharmacokinetics and pharmacogenetics of Gemcitabine as a mainstay in adult and pediatric oncology: an EORTC-PAMM perspective. Cancer Chemother Pharmacol. 2016 Jul;78(1):1-12. doi: 10.1007/s00280-016-3003-0. Epub 2016 Mar 23. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Ribosomal small subunit binding
- Specific Function
- Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-sit...
- Gene Name
- NME1
- Uniprot ID
- P15531
- Uniprot Name
- Nucleoside diphosphate kinase A
- Molecular Weight
- 17148.635 Da
References
- Ciccolini J, Serdjebi C, Peters GJ, Giovannetti E: Pharmacokinetics and pharmacogenetics of Gemcitabine as a mainstay in adult and pediatric oncology: an EORTC-PAMM perspective. Cancer Chemother Pharmacol. 2016 Jul;78(1):1-12. doi: 10.1007/s00280-016-3003-0. Epub 2016 Mar 23. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Bergman AM, Pinedo HM, Talianidis I, Veerman G, Loves WJ, van der Wilt CL, Peters GJ: Increased sensitivity to gemcitabine of P-glycoprotein and multidrug resistance-associated protein-overexpressing human cancer cell lines. Br J Cancer. 2003 Jun 16;88(12):1963-70. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Atpase activity, coupled to transmembrane movement of substances
- Specific Function
- ATP-dependent transporter probably involved in cellular detoxification through lipophilic anion extrusion.
- Gene Name
- ABCC10
- Uniprot ID
- Q5T3U5
- Uniprot Name
- Multidrug resistance-associated protein 7
- Molecular Weight
- 161627.375 Da
References
- Hopper-Borge E, Xu X, Shen T, Shi Z, Chen ZS, Kruh GD: Human multidrug resistance protein 7 (ABCC10) is a resistance factor for nucleoside analogues and epothilone B. Cancer Res. 2009 Jan 1;69(1):178-84. doi: 10.1158/0008-5472.CAN-08-1420. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Nucleoside transmembrane transporter activity
- Specific Function
- Mediates both influx and efflux of nucleosides across the membrane (equilibrative transporter). It is sensitive (ES) to low concentrations of the inhibitor nitrobenzylmercaptopurine riboside (NBMPR...
- Gene Name
- SLC29A1
- Uniprot ID
- Q99808
- Uniprot Name
- Equilibrative nucleoside transporter 1
- Molecular Weight
- 50218.805 Da
References
- Santini D, Vincenzi B, Fratto ME, Perrone G, Lai R, Catalano V, Cass C, Ruffini PA, Spoto C, Muretto P, Rizzo S, Muda AO, Mackey JR, Russo A, Tonini G, Graziano F: Prognostic role of human equilibrative transporter 1 (hENT1) in patients with resected gastric cancer. J Cell Physiol. 2010 May;223(2):384-8. doi: 10.1002/jcp.22045. [Article]
- Marce S, Molina-Arcas M, Villamor N, Casado FJ, Campo E, Pastor-Anglada M, Colomer D: Expression of human equilibrative nucleoside transporter 1 (hENT1) and its correlation with gemcitabine uptake and cytotoxicity in mantle cell lymphoma. Haematologica. 2006 Jul;91(7):895-902. [Article]
- Wang H, Word BR, Lyn-Cook BD: Enhanced efficacy of gemcitabine by indole-3-carbinol in pancreatic cell lines: the role of human equilibrative nucleoside transporter 1. Anticancer Res. 2011 Oct;31(10):3171-80. [Article]
- Morinaga S, Nakamura Y, Watanabe T, Mikayama H, Tamagawa H, Yamamoto N, Shiozawa M, Akaike M, Ohkawa S, Kameda Y, Miyagi Y: Immunohistochemical analysis of human equilibrative nucleoside transporter-1 (hENT1) predicts survival in resected pancreatic cancer patients treated with adjuvant gemcitabine monotherapy. Ann Surg Oncol. 2012 Jul;19 Suppl 3:S558-64. doi: 10.1245/s10434-011-2054-z. Epub 2011 Sep 13. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- General Function
- Pyrimidine- and adenine-specific:sodium symporter activity
- Specific Function
- Sodium-dependent and pyrimidine-selective. Exhibits the transport characteristics of the nucleoside transport system cit or N2 subtype (N2/cit) (selective for pyrimidine nucleosides and adenosine)....
- Gene Name
- SLC28A1
- Uniprot ID
- O00337
- Uniprot Name
- Sodium/nucleoside cotransporter 1
- Molecular Weight
- 71583.18 Da
References
- Mackey JR, Yao SY, Smith KM, Karpinski E, Baldwin SA, Cass CE, Young JD: Gemcitabine transport in xenopus oocytes expressing recombinant plasma membrane mammalian nucleoside transporters. J Natl Cancer Inst. 1999 Nov 3;91(21):1876-81. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- General Function
- Nucleoside transmembrane transporter activity
- Specific Function
- Mediates equilibrative transport of purine, pyrimidine nucleosides and the purine base hypoxanthine. Very less sensitive than SLC29A1 to inhibition by nitrobenzylthioinosine (NBMPR), dipyridamole, ...
- Gene Name
- SLC29A2
- Uniprot ID
- Q14542
- Uniprot Name
- Equilibrative nucleoside transporter 2
- Molecular Weight
- 50112.335 Da
References
- Mackey JR, Yao SY, Smith KM, Karpinski E, Baldwin SA, Cass CE, Young JD: Gemcitabine transport in xenopus oocytes expressing recombinant plasma membrane mammalian nucleoside transporters. J Natl Cancer Inst. 1999 Nov 3;91(21):1876-81. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Pyrimidine- and adenine-specific:sodium symporter activity
- Specific Function
- Sodium-dependent, pyrimidine- and purine-selective. Involved in the homeostasis of endogenous nucleosides. Exhibits the transport characteristics of the nucleoside transport system cib or N3 subtyp...
- Gene Name
- SLC28A3
- Uniprot ID
- Q9HAS3
- Uniprot Name
- Solute carrier family 28 member 3
- Molecular Weight
- 76929.61 Da
References
- Govindarajan R, Leung GP, Zhou M, Tse CM, Wang J, Unadkat JD: Facilitated mitochondrial import of antiviral and anticancer nucleoside drugs by human equilibrative nucleoside transporter-3. Am J Physiol Gastrointest Liver Physiol. 2009 Apr;296(4):G910-22. doi: 10.1152/ajpgi.90672.2008. Epub 2009 Jan 22. [Article]
Drug created on June 13, 2005 13:24 / Updated on September 28, 2021 07:54